Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime
| Autor: | Krstić Natalija M., Bjelaković Mira S., Dabović Milan M., Lorenc Ljubinka B., Pavlović Vladimir D. |
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| Jazyk: | angličtina |
| Rok vydání: | 2004 |
| Předmět: | |
| Zdroj: | Journal of the Serbian Chemical Society, Vol 69, Iss 6, Pp 413-420 (2004) |
| Druh dokumentu: | article |
| ISSN: | 0352-5139 1820-7421 |
| DOI: | 10.2298/JSC0406413K |
| Popis: | Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e. 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7%). |
| Databáze: | Directory of Open Access Journals |
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